In Hemingway's shadow: A road trip to Key West: Part I

Having coffee this morning at a hotel in Tuscany, I was greeted by a familiar sight: It was an article about Ernest Hemingway. Specifically, it was a sidebar in this month’s National Geographic about Hemingway’s house in Key West and the 50 cats that reside there.

It was familiar because the man is simply inescapable. I’ve spent the better part of eight years living abroad, mostly working as a correspondent in Italy and France - which is to say, spending a lot of time in hotels, cafes and bars - and so it’s hardly surprising that most places I go there is a waiter or hotelier who remarks, "You know, Hemingway spent some time here."  At the very least, there is a plaque to that effect or a photo of him on the wall.

Hemingway’s legacy pops up along the route of every traveler to Europe, and even shadows those in search of a life of leisure in the U.S. When visiting family in Florida, our default road trip is usually to the Keys, and at the end of the line is always Hemingway's home. It is a fitting terminus for any pilgrimage of pleasure that includes fishing, exploring and leisurely cocktails by the sea - and it’s about as close to an exotic island vacation as one can get without ever leaving the Lower 48.

For most travelers, this itinerary starts in Miami, and the initial stretch of U.S. Route 1 is nothing if not a modern rendition of Hemingway’s short story, "To Have and Have Not." Instead of the contrast between yacht owners and petty booze smugglers in Key West, the divide here is between the mansions of Miami’s southern suburbs and the ensuing impoverished wreck that is Dade City, and that continues all the way down to Key Largo.

My father grew up in the Chicago suburbs - not far, actually, from where Hemingway grew up in Oak Park - and the entrance to these islands, for him, always brought back memories of the 1948 gangster film "Key Largo", in which a hurricane devastates the area. "The bridge is out at Upper Matecumbe," he would say in his best Florida sheriff’s voice, driving across the modern drawbridge that separates mainland Florida from the string of islands.

At the other side of the bridge is Key Largo, the adjacent coral reef of John Pennekamp State Park and the sprawl of dive shops there ready to take you out on an adventure. That’s where I was certified as a diver, and I will never forget the first breath I took underwater there at a hotel pool, or following the anchor line down on my introductory, terrifying dive, my first meeting with barracuda, and orange-and-green moray eels popping out of the coral, or that satisfying taste of salt in my mouth on the sunset cruise back into the harbor, after becoming, at last, a SCUBA diver.

Of course, the first thing you want to do after slipping out of your wet dive gear is to find a cold beer, or better, a rum runner - the frozen drink that is synonymous with the Keys - and there are a few good Tiki bars to find them in Islamorada, as I discovered on Spring Break back in the 90s.

The other Florida Key lesson I had on that trip was the taste of yellow-fin tuna, which you caught that day on a charter boat and then brought back to one of the Islamorada restaurants. The chefs will cook it up for you for just a few dollars, and throw in some French fries as well - the assumption being that you’ll accompany your fresh catch with a few of their cold drinks, which, is a pretty good assumption.

Another option, for those with less time, is to have someone else catch the fish for you. Possibly the best fish restaurant in the world, in the opinion of someone who has tried quite a few of them, is to be found on the docks of the Islamorada Fish Company. There, you can dive into a basket of fresh grouper, mahi-mahi or snapper, seated on a lagoon-side deck under the glow of tiki torches.

Pull up a hammock at one of the beachside hotels and nap off the snapper and rum until the faint glow of morning comes over the water. You’re going to need a good night of sleep, because the best part of the Keys, and the most historic part of Hemingway’s old haunts, are still a few dozen miles down the road.

John Moretti is a freelance travel writer who divides his time between Europe, Florida and Vermont. He is the author of "Living Abroad in Italy" (Avalon, 2004) as well as a number of guidebooks. He writes about European sports and culture for the New York Sun.

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